Vacation Packages Under $999 | All Inclusive Packages to the Caribbean, Mexico, Punta Cana and Jamaica for less than $999

Tropical Deluxe Princess

All Inclusive

Tropical Deluxe Room

Montreal to Punta Cana, Dominican Republic Nov 07, 2021 (7 days)

Nov 07, 2021 (7 days) Tropical Deluxe Room

Get 37 Miles

was $1,995 Save 63%

$745PP

taxes & fees

Grand Park Royal Cozumel

All Inclusive

Deluxe Nature View

Montreal to Cozumel, Mexico Nov 23, 2021 (7 days)

Nov 23, 2021 (7 days) Deluxe Nature View

Get 39 Miles

was $1,892 Save 58%

$789PP

taxes & fees

Sol Palmeras

All Inclusive

Room

Montreal to Varadero, Cuba Oct 30, 2021 (7 days)

Oct 30, 2021 (7 days) Room

Get 35 Miles

was $1,475 Save 51%

$719PP

taxes & fees

Barcelo Solymar

All Inclusive

Bungalow Superior

Toronto to Varadero, Cuba Nov 27, 2021 (7 days)

Nov 27, 2021 (7 days) Bungalow Superior

Get 35 Miles

was $1,389 Save 49%

$709PP

taxes & fees

Vista Sol Punta Cana

All Inclusive

Pool View Room

Montreal to Punta Cana, Dominican Republic Oct 29, 2021 (7 days)

Oct 29, 2021 (7 days) Pool View Room

Get 35 Miles

was $1,325 Save 47%

$705PP

taxes & fees

Sheraton Bijao Beach Resort

All Inclusive

Deluxe Gardenview

Montreal to Playa Blanca Dec 17, 2021 (7 days)

Book with Deposit

Dec 17, 2021 (7 days) Deluxe Gardenview

Get 47 Miles

was $1,815 Save 47%

$955PP

taxes & fees

Book with Deposit

Bahia Principe Grand Tulum

All Inclusive

Junior Suite

Toronto to Riviera Maya, Mexico Oct 18, 2021 (7 days)

Oct 18, 2021 (7 days) Junior Suite

Get 38 Miles

was $1,239 Save 38%

$769PP

taxes & fees

El Cid Granada Mazatlan

All Inclusive

Studio

Toronto to Mazatlan, Mexico Nov 30, 2021 (7 days)

Nov 30, 2021 (7 days) Studio

Get 48 Miles

was $1,045

$975PP

taxes & fees

El Cozumeleno

All Inclusive

Room Gardenview

Toronto to Cozumel, Mexico Mar 22, 2022 (7 days)

Book with Deposit

Mar 22, 2022 (7 days) Room Gardenview

Get 46 Miles

$939PP

taxes & fees

Book with Deposit

Doubletree At The Entrance Universal Orlando

No Meals/Drinks

Room

Toronto to Orlando, Florida Apr 18, 2022 (7 days)

Book with Deposit

Apr 18, 2022 (7 days) Room

Get 39 Miles

$780PP

taxes & fees

Book with Deposit

Cassidys Hotel

No Meals/Drinks

Double Room

Toronto to Dublin, Ireland Jan 20, 2022 (8 days)

Book with Deposit

Jan 20, 2022 (8 days) Double Room

Get 43 Miles

$864PP

taxes & fees

Book with Deposit

The Bonnington Dublin

No Meals/Drinks

Classic Room Twin

Toronto to Dublin, Ireland Nov 13, 2021 (8 days)

Nov 13, 2021 (8 days) Classic Room Twin

Get 44 Miles

$891PP

taxes & fees

Mexico: Acapulco Cancun Los Cabos Puerto Vallarta Riviera Maya

Catalonia Riviera Maya And Yucatan Beach

All Inclusive

Room Gardenview

Toronto to Riviera Maya, Mexico Oct 21, 2021 (7 days)

Oct 21, 2021 (7 days) Room Gardenview

Get 35 Miles

was $1,719 Save 59%

$708PP

taxes & fees

Ocean Riviera Paradise

All Inclusive

Junior Suite

Toronto to Riviera Maya, Mexico Oct 18, 2021 (7 days)

Oct 18, 2021 (7 days) Junior Suite

Get 35 Miles

was $1,549 Save 54%

$719PP

taxes & fees

Royalton Riviera Cancun Resort And Spa

All Inclusive

Luxury Junior Suite

Toronto to Riviera Maya, Mexico Oct 20, 2021 (7 days)

Oct 20, 2021 (7 days) Luxury Junior Suite

Get 48 Miles

was $1,949 Save 50%

$968PP

taxes & fees

Iberostar Quetzal

All Inclusive

Double Room

Toronto to Riviera Maya, Mexico Oct 20, 2021 (7 days)

Oct 20, 2021 (7 days) Double Room

Get 47 Miles

was $1,759 Save 46%

$958PP

taxes & fees

Sunscape Akumal Beach Resort And Spa

All Inclusive

Deluxe Jungle View Double

Toronto to Riviera Maya, Mexico Nov 23, 2021 (7 days)

Nov 23, 2021 (7 days) Deluxe Jungle View Double

Get 41 Miles

was $1,390 Save 40%

$839PP

taxes & fees

Bahia Principe Luxury Akumal

All Inclusive

Junior Suite Superior

Toronto to Riviera Maya, Mexico Oct 18, 2021 (7 days)

Oct 18, 2021 (7 days) Junior Suite Superior

Get 42 Miles

was $1,329 Save 36%

$849PP

taxes & fees

The Fives Beach Hotel And Residences

All Inclusive

Upgrade To 1 Bedroom Suite Run Of The House

Toronto to Riviera Maya, Mexico Oct 19, 2021 (7 days)

Oct 19, 2021 (7 days) Upgrade To 1 Bedroom Suite Run Of The House

Get 46 Miles

was $1,439 Save 35%

$939PP

taxes & fees

Ocean Riviera Paradise El Beso

All Inclusive

El Beso Junior Suite Pool View Adults Only

Toronto to Riviera Maya, Mexico Oct 19, 2021 (7 days)

Oct 19, 2021 (7 days) El Beso Junior Suite Pool View Adults Only

Get 46 Miles

was $1,389 Save 33%

$929PP

taxes & fees

Iberostar Paraiso Beach

All Inclusive

Double Room

Toronto to Riviera Maya, Mexico Oct 18, 2021 (7 days)

Oct 18, 2021 (7 days) Double Room

Get 45 Miles

was $1,359 Save 32%

$919PP

taxes & fees

Riu Playacar

All Inclusive

Room

Toronto to Riviera Maya, Mexico Oct 15, 2021 (7 days)

Oct 15, 2021 (7 days) Room

Get 47 Miles

was $1,385 Save 31%

$955PP

taxes & fees

Cuba: Cayo Coco Cayo Largo Havana Holguin Varadero

Pullman Cayo Coco

All Inclusive

Deluxe Gardenview

Montreal to Cayo Coco, Cuba Oct 23, 2021 (7 days)

Oct 23, 2021 (7 days) Deluxe Gardenview

Get 35 Miles

was $1,855 Save 62%

$705PP

taxes & fees

Gran Muthu Imperial

All Inclusive

Room

Montreal to Cayo Coco, Cuba Nov 15, 2021 (7 days)

Nov 15, 2021 (7 days) Room

Get 35 Miles

was $1,735 Save 59%

$719PP

taxes & fees

Hotel Colonial Cayo Coco

All Inclusive

Supersaver Room

Montreal to Cayo Coco, Cuba Jan 13, 2022 (7 days)

Book with Deposit

Jan 13, 2022 (7 days) Supersaver Room

Get 34 Miles

was $1,317 Save 47%

$699PP

taxes & fees

Book with Deposit

Hotel Mojito

All Inclusive

Room

Toronto to Cayo Coco, Cuba Nov 17, 2021 (7 days)

Nov 17, 2021 (7 days) Room

Get 35 Miles

was $1,085 Save 35%

$705PP

taxes & fees

Iberostar Selection Playa Pilar

All Inclusive

Room

Toronto to Cayo Coco, Cuba Apr 15, 2022 (7 days)

Book with Deposit

Apr 15, 2022 (7 days) Room

Get 40 Miles

was $1,249 Save 34%

$819PP

taxes & fees

Book with Deposit

Grand Muthu Cayo Guillermo

All Inclusive

Room

Ottawa to Cayo Coco, Cuba Nov 02, 2021 (7 days)

Nov 02, 2021 (7 days) Room

Get 35 Miles

$709PP

taxes & fees

Hotel Playa Paraiso

All Inclusive

Room

Ottawa to Cayo Coco, Cuba Nov 02, 2021 (7 days)

Nov 02, 2021 (7 days) Room

Get 35 Miles

$719PP

taxes & fees

Tryp Cayo Coco

All Inclusive

Tryp Room

Ottawa to Cayo Coco, Cuba Nov 02, 2021 (7 days)

Nov 02, 2021 (7 days) Tryp Room

Get 35 Miles

$719PP

taxes & fees

Gran Muthu Rainbow Cayo Guillermo

All Inclusive

Junior Suite

Toronto to Cayo Coco, Cuba Nov 02, 2021 (7 days)

Nov 02, 2021 (7 days) Junior Suite

Get 36 Miles

$729PP

taxes & fees

Melia Jardines Del Rey

All Inclusive

Room

Toronto to Cayo Coco, Cuba Apr 12, 2022 (7 days)

Book with Deposit

Apr 12, 2022 (7 days) Room

Get 35 Miles

$709PP

taxes & fees

Book with Deposit

Dominican Republic: La Romana Puerto Plata Punta Cana Samana Santo Domingo

Viva Wyndham Dominicus Palace

All Inclusive

Superior Room

Toronto to La Romana, Dominican Republic Oct 14, 2021 (7 days)

Oct 14, 2021 (7 days) Superior Room

Get 36 Miles

was $1,775 Save 59%

$735PP

taxes & fees

Be Live Collection Canoa Adults Club

All Inclusive

Junior Suite

Toronto to La Romana, Dominican Republic Nov 02, 2021 (7 days)

Nov 02, 2021 (7 days) Junior Suite

Get 39 Miles

was $1,929 Save 59%

$799PP

taxes & fees

Viva Wyndham V Samana

All Inclusive

V Room

Montreal to Samana, Dominican Republic Oct 25, 2021 (7 days)

Oct 25, 2021 (7 days) V Room

Get 37 Miles

was $1,608 Save 53%

$749PP

taxes & fees

Bahia Principe Grand El Portillo

All Inclusive

Room

Montreal to Samana, Dominican Republic Oct 25, 2021 (7 days)

Oct 25, 2021 (7 days) Room

Get 37 Miles

was $1,598 Save 53%

$749PP

taxes & fees

Be Live Collection Canoa

All Inclusive

Deluxe Room

Montreal to La Romana, Dominican Republic Oct 28, 2021 (7 days)

Oct 28, 2021 (7 days) Deluxe Room

Get 37 Miles

was $1,386 Save 45%

$759PP

taxes & fees

Bahia Principe Grand La Romana

All Inclusive

Junior Suite Superior

Montreal to La Romana, Dominican Republic Apr 22, 2022 (7 days)

Book with Deposit

Apr 22, 2022 (7 days) Junior Suite Superior

Get 48 Miles

was $1,712 Save 43%

$969PP

taxes & fees

Book with Deposit

Whala Bayahibe

All Inclusive

Room

Toronto to La Romana, Dominican Republic Oct 27, 2021 (7 days)

Oct 27, 2021 (7 days) Room

Get 35 Miles

was $1,095 Save 36%

$705PP

taxes & fees

Bahia Principe Luxury Samana

All Inclusive

Superior Room No Balcony

Toronto to Samana, Dominican Republic Apr 23, 2022 (7 days)

Book with Deposit

Apr 23, 2022 (7 days) Superior Room No Balcony

Get 49 Miles

was $1,479 Save 33%

$989PP

taxes & fees

Book with Deposit

Grand Paradise Samana

All Inclusive

Deluxe Gardenview

Toronto to Samana, Dominican Republic Apr 23, 2022 (7 days)

Book with Deposit

Apr 23, 2022 (7 days) Deluxe Gardenview

Get 34 Miles

was $1,009 Save 31%

$699PP

taxes & fees

Book with Deposit

Bahia Principe Luxury Bouganville

All Inclusive

Junior Suite Deluxe

Toronto to La Romana, Dominican Republic Nov 04, 2021 (7 days)

Nov 04, 2021 (7 days) Junior Suite Deluxe

Get 48 Miles

was $1,329 Save 27%

$969PP

taxes & fees

Jamaica: Whitehouse Montego Bay Negril Ocho Rios Runaway Bay

Fun Holiday Beach Resort

All Inclusive

Room

Toronto to Negril, Jamaica Nov 19, 2021 (7 days)

Nov 19, 2021 (7 days) Room

Get 36 Miles

was $1,389 Save 48%

$729PP

taxes & fees

Deja Resort

All Inclusive

Room

Toronto to Montego Bay, Jamaica Oct 20, 2021 (7 days)

Oct 20, 2021 (7 days) Room

Get 47 Miles

was $1,645 Save 42%

$955PP

taxes & fees

Royal Decameron Cornwall Beach

All Inclusive

Room

Toronto to Montego Bay, Jamaica Nov 19, 2021 (7 days)

Nov 19, 2021 (7 days) Room

Get 47 Miles

was $1,629 Save 41%

$959PP

taxes & fees

Royal Decameron Montego Beach

All Inclusive

Room Gardenview

Toronto to Montego Bay, Jamaica Oct 20, 2021 (7 days)

Oct 20, 2021 (7 days) Room Gardenview

Get 45 Miles

was $1,495 Save 39%

$915PP

taxes & fees

Rondel Village

No Meals/Drinks

Room Gardenview

Toronto to Negril, Jamaica Oct 27, 2021 (7 days)

Oct 27, 2021 (7 days) Room Gardenview

Get 44 Miles

was $1,365 Save 34%

$895PP

taxes & fees

Samsara Cliff Resort And Spa

No Meals/Drinks

Gardenview Room

Toronto to Negril, Jamaica Nov 03, 2021 (7 days)

Nov 03, 2021 (7 days) Gardenview Room

Get 35 Miles

$705PP

taxes & fees

Legends Beach Resort

No Meals/Drinks

Room

Toronto to Negril, Jamaica Nov 03, 2021 (7 days)

Nov 03, 2021 (7 days) Room

Get 36 Miles

$735PP

taxes & fees

Holiday Inn Resort Montego Bay

All Inclusive

Room

Toronto to Montego Bay, Jamaica Oct 21, 2021 (7 days)

Oct 21, 2021 (7 days) Room

Get 44 Miles

$899PP

taxes & fees

Caribbean: Turks & Caicos Aruba Antigua Nassau Barbados

Eagle Aruba Resort And Casino

No Meals/Drinks

1 Bedroom Premium Suite

Toronto to Aruba, Caribbean Oct 18, 2021 (7 days)

Oct 18, 2021 (7 days) 1 Bedroom Premium Suite

Get 40 Miles

was $2,465 Save 67%

$815PP

taxes & fees

Hawksbill By Rex Resort

All Inclusive

Bungalow Gardenview

Toronto to Antigua, Caribbean Oct 17, 2021 (7 days)

Oct 17, 2021 (7 days) Bungalow Gardenview

Get 48 Miles

was $1,679 Save 42%

$969PP

taxes & fees

Acoya Curacao Resort Villas And Spa

No Meals/Drinks

Standard Room

Montreal to Curacao Oct 15, 2021 (7 days)

Oct 15, 2021 (7 days) Standard Room

Get 36 Miles

$729PP

taxes & fees

Florida: Tampa Bay Orlando Miami Fort Meyers Fort Lauderdale

Ocean Sky Hotel And Resort

No Meals/Drinks

Room

Toronto to Fort Lauderdale, Florida Dec 04, 2021 (7 days)

Dec 04, 2021 (7 days) Room

Get 36 Miles

$732PP

taxes & fees

Hawaii: Honolulu Maui Kailua/Kona

Ohia Waikiki Studio Suites

No Meals/Drinks

City View With Kitchen 2 Double

Vancouver to Honolulu, Hawaii Nov 11, 2021 (7 days)

Nov 11, 2021 (7 days) City View With Kitchen 2 Double

Get 37 Miles

was $1,960 Save 62%

$749PP

taxes & fees

Aston Waikiki Circle

No Meals/Drinks

Standard View Room

Vancouver to Honolulu, Hawaii Nov 20, 2021 (7 days)

Nov 20, 2021 (7 days) Standard View Room

Get 41 Miles

was $1,973 Save 57%

$839PP

taxes & fees

Aqua Skyline At Island Colony

No Meals/Drinks

Studio Kitchenette

Vancouver to Honolulu, Hawaii Oct 23, 2021 (7 days)

Oct 23, 2021 (7 days) Studio Kitchenette

Get 37 Miles

was $1,734 Save 57%

$749PP

taxes & fees

Aston At The Waikiki Banyan

No Meals/Drinks

1 Bedroom Standard Suite

Vancouver to Honolulu, Hawaii Oct 23, 2021 (7 days)

Oct 23, 2021 (7 days) 1 Bedroom Standard Suite

Get 40 Miles

was $1,702 Save 52%

$819PP

taxes & fees

Ohana Waikiki East By Outrigger

No Meals/Drinks

Room King

Vancouver to Honolulu, Hawaii Oct 23, 2021 (7 days)

Oct 23, 2021 (7 days) Room King

Get 39 Miles

was $1,497 Save 47%

$789PP

taxes & fees

Pacific Monarch Hotel

No Meals/Drinks

Partial Oceanview Studio 1 Queen

Vancouver to Honolulu, Hawaii Nov 29, 2021 (7 days)

Nov 29, 2021 (7 days) Partial Oceanview Studio 1 Queen

Get 35 Miles

was $1,309 Save 46%

$709PP

taxes & fees

Aston Waikiki Beach Hotel

No Meals/Drinks

Partial Oceanview Room King

Vancouver to Honolulu, Hawaii Nov 05, 2021 (7 days)

Nov 05, 2021 (7 days) Partial Oceanview Room King

Get 48 Miles

was $1,739 Save 44%

$979PP

taxes & fees

Waikiki Malia By Outrigger

No Meals/Drinks

Waikiki View Room King

Vancouver to Honolulu, Hawaii Nov 29, 2021 (7 days)

Nov 29, 2021 (7 days) Waikiki View Room King

Get 38 Miles

was $1,080 Save 28%

$779PP

taxes & fees

Sheraton Princess Kaiulani

No Meals/Drinks

Kaiulani Room

Vancouver to Honolulu, Hawaii Nov 29, 2021 (7 days)

Nov 29, 2021 (7 days) Kaiulani Room

Get 42 Miles

was $1,159 Save 26%

$859PP

taxes & fees

Aston Waikiki Sunset

No Meals/Drinks

1 Bedroom Suite

Vancouver to Honolulu, Hawaii Oct 15, 2021 (7 days)

Oct 15, 2021 (7 days) 1 Bedroom Suite

Get 43 Miles

$879PP

taxes & fees

Harrahs

No Meals/Drinks

Deluxe Room King Non Smoking

Calgary to Las Vegas, Nevada Apr 02, 2022 (7 days)

Book with Deposit

Apr 02, 2022 (7 days) Deluxe Room King Non Smoking

Get 35 Miles

was $923 Save 24%

$706PP

taxes & fees

Book with Deposit

Oyo Hotel And Casino

No Meals/Drinks

Room King

Ottawa to Las Vegas, Nevada Nov 26, 2021 (7 days)

Nov 26, 2021 (7 days) Room King

Get 35 Miles

was $812 Save 12%

$716PP

taxes & fees

Park Mgm Las Vegas

No Meals/Drinks

Park Mgm King

Ottawa to Las Vegas, Nevada Nov 26, 2021 (7 days)

Nov 26, 2021 (7 days) Park Mgm King

Get 35 Miles

was $768

$703PP

taxes & fees

Rio All Suite Hotel And Las Vegas

No Meals/Drinks

Deluxe Suite King Mountain View Non Smoking

Winnipeg to Las Vegas, Nevada Nov 26, 2021 (7 days)

Nov 26, 2021 (7 days) Deluxe Suite King Mountain View Non Smoking

Get 36 Miles

was $779

$736PP

taxes & fees

Paris Las Vegas

No Meals/Drinks

Burgundy Room 2 Queen Non Smoking

Winnipeg to Las Vegas, Nevada Dec 15, 2021 (7 days)

Dec 15, 2021 (7 days) Burgundy Room 2 Queen Non Smoking

Get 35 Miles

was $737

$703PP

taxes & fees

Excalibur Hotel And Casino

No Meals/Drinks

Resort Tower 2 Queen Room

Ottawa to Las Vegas, Nevada Dec 10, 2021 (7 days)

Dec 10, 2021 (7 days) Resort Tower 2 Queen Room

Get 35 Miles

$705PP

taxes & fees

Westgate Las Vegas Resort And Casino

No Meals/Drinks

Premium Room

Ottawa to Las Vegas, Nevada Dec 10, 2021 (7 days)

Dec 10, 2021 (7 days) Premium Room

Get 35 Miles

$716PP

taxes & fees

Flamingo Las Vegas

No Meals/Drinks

Fab Room King Non Smoking

Ottawa to Las Vegas, Nevada Dec 10, 2021 (7 days)

Dec 10, 2021 (7 days) Fab Room King Non Smoking

Get 35 Miles

$716PP

taxes & fees

Treasure Island - Ti A Radisson Hotel

No Meals/Drinks

Deluxe Room Run Of The House

Ottawa to Las Vegas, Nevada Dec 10, 2021 (7 days)

Dec 10, 2021 (7 days) Deluxe Room Run Of The House

Get 37 Miles

$750PP

taxes & fees

Circus Circus Las Vegas

No Meals/Drinks

West Tower Room King Non Smoking

Winnipeg to Las Vegas, Nevada Nov 25, 2021 (7 days)

Nov 25, 2021 (7 days) West Tower Room King Non Smoking

Get 36 Miles

$735PP

taxes & fees

Vacation Deals Under $999

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Vacation Deals Under $999

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